Strapless Casual Maxi Dresses
Strapless casual maxi dresses are the ultimate power move for those days when you want to look effortlessly put-together without even trying. Whether you’re headed out with your crew or just vibing solo, these easy-breezy silhouettes have your back—no straps, no problem. Slip into a strapless casual maxi dress and watch how quickly you become the main character, turning every sidewalk into your runway. Because sometimes, the best kind of drama is in your outfit, not your group chat.
$34.90
A chic strapless brown maxi dress with a high slit and flattering bodycon silhouette.
$59.90
An ivory A-line maxi dress featuring gauze fabric, sheer lace insets, and a faux leather belt.
$42.90
A strapless black floral mesh maxi dress with a bodycon fit and high-side slit.
$39.90
A strapless black mesh maxi dress featuring a floral print, high side slit, and form-hugging silhouette.
$46.90
A strapless natural knit maxi dress featuring open-knit crochet, a twist neckline, and a curve-hugging fit.
$44.90
A strapless burgundy mesh maxi dress featuring a bold floral print and a dramatic high side slit.
$19.97 $34.90 43% off
A light blue strapless maxi dress featuring bold floral mesh, stretchy knit lining, and a curve-hugging fit.
$44.90
A black floral maxi dress featuring sheer mesh, a lace-up strappy back, and a form-hugging silhouette.
$15.97 $79.90 80% off
An elegant strapless satin dress in orange featuring a high ruffled slit and curve-hugging silhouette.
$35.90
A black knit maxi dress featuring a front keyhole cutout and a curve-hugging, textured silhouette.
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Achieve a perfectly stylish everyday look with this sleeveless ribbed knit midi dress! Designed with a comfortable ribbed knit fabric offering plenty of stretch, it features a V-neckline, spaghetti straps, a midi-length hem with a chic high front slit, and a form-hugging silhouette. Pair with a cropped denim jacket and clear mules. Fit & FeaturesStretchy ribbed knit fabric, V-neckline, Spaghetti straps, High front slit, Form-hugging fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Perfectly Stylish Sleeveless Ribbed Knit Midi Dress in Black | Size: M | Knit Fabric
Channel the chic fall vibe in this ditsy floral woven midi dress featuring a sleeveless sweetheart neckline with a ruched bust and tie-front detail, thin tank shoulder straps, and a corset-style bodice. The high waist leads to a flowy A-line silhouette accented with a high-cut front slit. Fit & FeaturesDitsy floral-printed woven fabric, Sweetheart neckline, ruched bust, tie-front detail, underwire bust, Thin tank shoulder straps, Corset-style bodice with piping, high waist seam, Hidden side zipper and hook-eye closure, High front slit, Midi-length A-line fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Chic Fall Vibe Ditsy Floral Corset Midi Dress in Brown | Size: S | Woven Fabric
Windsor Thriving Blooms Corset Floral Slit Midi Dress in Black
$20.97 $46.90
55% off
Thrive with sweet energy in this floral midi dress perfect for brunches or dates! With a corset bodice that snatches your waist and a flirty front slit, this a-line dress will captive everyone. Pair with a necklace. Fit & FeaturesDitsy floral print, woven fabric, Wide shoulder straps, sweetheart neckline, Corset bodice, Side pockets, A-line silhouette, front slit, Midi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Thriving Blooms Corset Floral Slit Midi Dress in Black | Size: S | Woven Fabric
Capture hearts with your sweet look in this airy eyelet knit skater dress. You'll adore the flowy feel of the fit-and-flare silhouette. Fit & FeaturesEyelet knit fabric with knit lining, Sleeveless square neckline, underbust seam, Adjustable spaghetti straps, Skater silhouette, Mini-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sweet Look Eyelet Knit Skater Dress in White | Size: M | Knit Fabric
Create a cute picturesque 'fit in this corset A-line midi dress! The corset bodice and lace-up back add a touch of allure to the sweet silhouette. Fit & FeaturesWoven fabric lined with stretchy knit, Sweetheart neckline, tie-front detail, Thin adjustable straps, Corset bodice, lace-up back, High waist seam, Midi-length A-line silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Picturesque Cutie Corset Lace-Up A-Line Midi Dress in Light Blue | Size: L | Woven Fabric
Show off your smooth moves in this strapless bodycon midi dress perfect for dressing up or down for any occasion! Fit & FeaturesRib knit fabric, sewn-in knit lining, moderate stretch, Strapless neckline, Side slit, Bodycon silhouette, Midi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Smooth Talker Strapless Bodycon Midi Dress in Light Blue | Size: L | Knit Fabric
This sleeveless ribbed knit midi dress features a striking V-neckline and bodycon fit with a front slit detail for movement. Perfect for layering with a jacket and heels. Fit & FeaturesStretchy ribbed knit fabric, V-neckline, Spaghetti straps, Front slit, Midi-length bodycon fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Toasty Sweetheart V-Neck Bodycon Knit Midi Dress in Chartreuse | Size: L | Knit Fabric
The perfect chic sleeveless midi dress for grabbing dinner downtown! Crafted from smooth knit fabric, this crew neck dress boasts curve-accentuating ruched seams along the bodycon silhouette and a sleek midi-length hem. Pair with kitten heels and a clutch. Fit & FeaturesSmooth knit fabric, stretchy knit lining, Sleeveless crew neck, Side ruched seams, Bodycon silhouette, Midi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Dinner Downtown Sleeveless Ruched Midi Dress in Brown | Size: M | Knit Fabric
On A Vacay Strapless Tropical Slit Maxi Dress
$19.97 $39.90
50% off
From sunny vacations to island getaways, this tropical maxi dress is destined to go with you on your next trip! Fit & FeaturesTropical palm print, mesh fabric lined with stretchy knit, Strapless neckline, Form-hugging silhouette, High side slit, Maxi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor On A Vacay Strapless Tropical Slit Maxi Dress | Size: XS | Mesh Fabric/Mesh Fabric
Windsor Blissful Cutie Halter Cutout Skater Dress in Yellow
$9.97 $46.90
79% off
Get swept off your feet in this cute skater dress for any casual occasion! With its halter neckline and cutout bodice, this dress is designed to show off your figure, while the ruffled mini-length hem adds a flirty touch. Fit & FeaturesGauze woven fabric, woven lining, Halter neckline with spaghetti strap ties, Stretchy smocked bust, Cutout bodice, Ruffled skater silhouette, Mini-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Blissful Cutie Halter Cutout Skater Dress in Yellow | Size: L | Gauze/Woven Fabric
Strapless Casual Maxi Dresses
When it comes to living your best life, nothing says “main character energy” quite like a strapless maxi dress that’s as easygoing as your group chat on a Friday night. The strapless maxi dress casual vibe is all about letting your shoulders catch a little sun, feeling that breeze swirl around your legs, and moving through your day with the kind of confidence that makes people wonder what your secret is. It’s your go-to for impromptu brunches, last-minute road trips, or those endless golden-hour hangs where every detail feels just right. Whether you’re styling it with chunky sneakers and a denim jacket for that off-duty model look, or slipping into strappy sandals and stacking on the jewelry for a rooftop soirée, a strapless casual maxi dress is basically your wardrobe’s version of a “don’t worry, I got you” text. You’ll love how it flatters every curve, giving you that effortless, flowy silhouette that’s both comfy and totally Insta-worthy. And if you’re the queen of gifting, trust: a strapless maxi dress is the kind of present that makes birthdays, bachelorettes, or just-because surprises feel extra magical—because who doesn’t want to unwrap a piece that instantly upgrades their closet?
Your strapless maxi dress is the ultimate BFF—always down for whatever, never judging your snack choices, and ready to make you look fire with zero effort. It’s the piece you grab when you want to keep things low-key but still serve a little drama (hello, bare shoulders and swishy skirt!). If you’re packing for a weekend getaway, toss in a strapless maxi dress casual style and you’re set for everything from exploring cute little shops to late-night dancing under the stars. Pro tip: add a floppy hat and oversized sunnies for a look that’s pure main character, or throw on a leather jacket when the night gets a little wild. These dresses are also a dream for anyone who loves a one-and-done outfit—no matching required, just slip it on and go live your best life. And if you’re the type who likes to keep things versatile, you’ll love how easily a strapless maxi dress can transition from lounging around the house to running errands or even making an entrance at a dinner party. For those special “I do” moments, don’t miss our curated collection of Strapless Maxi Dresses For Weddings—because your RSVP deserves a look as unforgettable as the celebration.
Let’s be real, life is too short for boring outfits, and a strapless maxi dress is the answer when you want to feel unstoppable without breaking a sweat. It’s the kind of piece that works for everyone—your BFF who’s always down for an adventure, your sister who needs something cute for her next vacay, or even your mom who secretly loves a little glam. The best part? These dresses are built for good vibes and great memories, whether you’re twirling on the dance floor, picnicking in the park, or just soaking up the sun with your ride-or-die crew. So go ahead and make some trouble, break a few hearts, and take on the world—your strapless maxi dress will be right there with you, hyping you up every step of the way.